Book 2 Star Hotels in Sherwood
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Featured Sherwood 2 Stars Hotels

Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St Annapolis MD
Free Cancellation
Reserve now, pay when you stay
17.32 mi from city center
$212 nightly
The price is $241 total per night
$241 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
Annapolis Waterfront Hotel, Autograph Collection offers a 24-hour gym, a rooftop terrace, and free WiFi in public areas. Valet parking is available for USD 39 per day. The 24-hour front desk has staff standing by to help with concierge services, luggage storage, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include meeting rooms, conference space, and a 24-hour business center.
Pet friendly
Free WiFi

Historic Inns of Annapolis
58 State Circle Annapolis MD
Free Cancellation
Reserve now, pay when you stay
17.62 mi from city center
$169 nightly
The price is $193 total per night
$193 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
At Historic Inns of Annapolis, guests have access to a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is available for USD 50.00 per night, and there's also limo/town car service. The front desk has multilingual staff on hand 24/7 to help with securing valuables, tours or tickets, and luggage storage. Other amenities at this historic hotel include conference space, coffee/tea in a common area, and express check-in.
Pet friendly
Free WiFi

Graduate by Hilton Annapolis
126 West St Annapolis MD
Free Cancellation
Reserve now, pay when you stay
17.79 mi from city center
$150 nightly
The price is $171 total per night
$171 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Graduate by Hilton Annapolis features a 24-hour gym, free WiFi in public areas, and conference space. Valet parking is available for USD 39 per night. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include free use of bicycles, a ballroom, and an ATM.
Pet friendly
Free WiFi

Hilton Garden Inn Annapolis Downtown
174 West Street Annapolis MD
Free Cancellation
Reserve now, pay when you stay
17.81 mi from city center
$89 nightly
The price is $102 total per night
$102 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
Hilton Garden Inn Annapolis Downtown features a 24-hour gym, free WiFi in public areas, and conference space. Parking is available for USD 35 per night (USD 39 per night for valet parking), and there's also an area shuttle. The front desk has multilingual staff on hand 24/7 to help with luggage storage, dry cleaning/laundry, and securing valuables. Additional amenities include a business center, laundry facilities, and wedding services.
Pet friendly
Free WiFi

The Westin Annapolis
100 Westgate Cir Annapolis MD
Free Cancellation
Reserve now, pay when you stay
17.89 mi from city center
$139 nightly
The price is $158 total per night
$158 total
Dec 28 - Dec 29
Total with taxes and fees
At The Westin Annapolis, guests enjoy a full-service spa, an indoor pool, and a 24-hour gym. Valet parking is offered for USD 39 per night. Front-desk staff can answer questions 24/7, and assist with dry cleaning/laundry, concierge services, and luggage storage. Other amenities at this spa hotel include free WiFi in public areas, conference space, and a 24-hour business center.
Pool
Spa

Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
Free Cancellation
Reserve now, pay when you stay
20.07 mi from city center
$197 nightly
The price is $224 total per night
$224 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Hyatt Regency Chesapeake Bay features a private beach, a golf course, and a marina. A stay here includes free parking. Multilingual staff at the front desk are standing by 24/7 to help with luggage storage, tours or tickets, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include a full-service spa, 2 outdoor pools, and an indoor pool.
On private beach
Pool

Hampton Inn & Suites Annapolis
124 Womack Dr Annapolis MD
Free Cancellation
Reserve now, pay when you stay
19.25 mi from city center
$81 nightly
The price is $93 total per night
$93 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
At Hampton Inn & Suites Annapolis, guests have access to a gym, free WiFi in public areas, and meeting rooms. Self parking is available for USD 10 per night. Multilingual staff at the 24-hour front desk can assist with dry cleaning/laundry, securing valuables, and luggage storage. Other amenities at this family-friendly hotel include conference space, a 24-hour business center, and a seasonal outdoor pool.
Pool
Breakfast included

DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Free Cancellation
Reserve now, pay when you stay
19.5 mi from city center
$75 nightly
The price is $85 total per night
$85 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guests of DoubleTree by Hilton Hotel Annapolis enjoy a 24-hour gym, free WiFi in public areas, and conference space. There's free parking and a free area shuttle. The 24-hour front desk has multilingual staff ready to assist with luggage storage and dry cleaning/laundry. Additional amenities include a business center, a microwave in a common area, and a refrigerator in a common area.
Pet friendly
Parking included

Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
Free Cancellation
19.68 mi from city center
$106 nightly
The price is $121 total per night
$121 total
Jan 25 - Jan 26, 2026
Total with taxes and fees
At Crowne Plaza Annapolis by IHG, guests enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. You can take advantage of free parking if you drive. The 24-hour front desk has staff standing by to help with dry cleaning/laundry and luggage storage. Additional amenities include meeting rooms, conference space, and a business center.
Pool
Parking included
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Sherwood hotels essential information
Accommodation | 1,150 hotels |
|---|---|
Lowest Price | $85 |
Highest Price | $241 |
Popular hotels | DoubleTree by Hilton Hotel Annapolis, Historic Inns of Annapolis, Crowne Plaza Annapolis by IHG, Graduate by Hilton Annapolis, Hilton Garden Inn Annapolis Downtown, Annapolis Waterfront Hotel, Autograph Collection, Hyatt Regency Chesapeake Bay, Hampton Inn & Suites Annapolis, The Westin Annapolis |
Recent Reviews

Historic Inns of Annapolis
5/5 Excellent
"Best place to stay is the main building"
A verified traveler from Palm City stayed at Historic Inns of Annapolis
Posted 5 days ago


